ES2767898T3 - Proceso para la preparación de una amina quiral ópticamente activa - Google Patents
Proceso para la preparación de una amina quiral ópticamente activa Download PDFInfo
- Publication number
- ES2767898T3 ES2767898T3 ES10002780T ES10002780T ES2767898T3 ES 2767898 T3 ES2767898 T3 ES 2767898T3 ES 10002780 T ES10002780 T ES 10002780T ES 10002780 T ES10002780 T ES 10002780T ES 2767898 T3 ES2767898 T3 ES 2767898T3
- Authority
- ES
- Spain
- Prior art keywords
- reaction
- process according
- amino
- transaminase
- pdc
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000000034 method Methods 0.000 title claims description 60
- 150000001412 amines Chemical class 0.000 title claims description 40
- 238000002360 preparation method Methods 0.000 title claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 143
- 108010011939 Pyruvate Decarboxylase Proteins 0.000 claims description 72
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 64
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 54
- 102000003929 Transaminases Human genes 0.000 claims description 53
- 108090000340 Transaminases Proteins 0.000 claims description 53
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 235000004279 alanine Nutrition 0.000 claims description 28
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims description 24
- 229940076788 pyruvate Drugs 0.000 claims description 24
- 150000002576 ketones Chemical class 0.000 claims description 23
- 239000011541 reaction mixture Substances 0.000 claims description 23
- 102000004190 Enzymes Human genes 0.000 claims description 20
- 108090000790 Enzymes Proteins 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000006227 byproduct Substances 0.000 claims description 10
- 102000003855 L-lactate dehydrogenase Human genes 0.000 claims description 9
- 108700023483 L-lactate dehydrogenases Proteins 0.000 claims description 9
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 8
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 8
- BTNMPGBKDVTSJY-UHFFFAOYSA-N keto-phenylpyruvic acid Chemical group OC(=O)C(=O)CC1=CC=CC=C1 BTNMPGBKDVTSJY-UHFFFAOYSA-N 0.000 claims description 8
- -1 p-aminobutyrate Chemical compound 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 6
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 5
- NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical compound NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 claims description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 4
- 239000001903 2-oxo-3-phenylpropanoic acid Substances 0.000 claims description 4
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 claims description 4
- 229930186147 Cephalosporin Natural products 0.000 claims description 4
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 4
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 claims description 4
- DEDGUGJNLNLJSR-UHFFFAOYSA-N alpha-hydroxycinnamic acid Natural products OC(=O)C(O)=CC1=CC=CC=C1 DEDGUGJNLNLJSR-UHFFFAOYSA-N 0.000 claims description 4
- 235000001014 amino acid Nutrition 0.000 claims description 4
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 229940124587 cephalosporin Drugs 0.000 claims description 4
- 150000001780 cephalosporins Chemical class 0.000 claims description 4
- HHIOOBJZIASBFF-UHFFFAOYSA-N ethyl 3-aminobutanoate Chemical compound CCOC(=O)CC(C)N HHIOOBJZIASBFF-UHFFFAOYSA-N 0.000 claims description 4
- XJMIXEAZMCTAGH-UHFFFAOYSA-N methyl 3-oxopentanoate Chemical compound CCC(=O)CC(=O)OC XJMIXEAZMCTAGH-UHFFFAOYSA-N 0.000 claims description 4
- QGKLPGKXAVVPOJ-UHFFFAOYSA-N pyrrolidin-3-one Chemical compound O=C1CCNC1 QGKLPGKXAVVPOJ-UHFFFAOYSA-N 0.000 claims description 4
- 229940107700 pyruvic acid Drugs 0.000 claims description 4
- CUZLJOLBIRPEFB-UHFFFAOYSA-N 1-methoxypropan-2-one Chemical compound COCC(C)=O CUZLJOLBIRPEFB-UHFFFAOYSA-N 0.000 claims description 3
- WEGYGNROSJDEIW-UHFFFAOYSA-N 3-Acetylpyridine Chemical compound CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-UHFFFAOYSA-N 0.000 claims description 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 3
- 229940067621 aminobutyrate Drugs 0.000 claims description 3
- 229930195712 glutamate Natural products 0.000 claims description 3
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 3
- USISRUCGEISZIB-UHFFFAOYSA-N piperidin-3-one Chemical compound O=C1CCCNC1 USISRUCGEISZIB-UHFFFAOYSA-N 0.000 claims description 3
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims description 3
- NXMXETCTWNXSFG-UHFFFAOYSA-N 1-methoxypropan-2-amine Chemical compound COCC(C)N NXMXETCTWNXSFG-UHFFFAOYSA-N 0.000 claims description 2
- LJCWONGJFPCTTL-UHFFFAOYSA-N 4-hydroxyphenylglycine Chemical compound OC(=O)C(N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-UHFFFAOYSA-N 0.000 claims description 2
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 claims description 2
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N Phosphinothricin Natural products CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 claims description 2
- CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 2
- IAJOBQBIJHVGMQ-BYPYZUCNSA-N glufosinate-P Chemical compound CP(O)(=O)CC[C@H](N)C(O)=O IAJOBQBIJHVGMQ-BYPYZUCNSA-N 0.000 claims description 2
- JNHZPXFARRJZQR-UHFFFAOYSA-N n-ethylpyridin-3-amine Chemical compound CCNC1=CC=CN=C1 JNHZPXFARRJZQR-UHFFFAOYSA-N 0.000 claims description 2
- PEUGKEHLRUVPAN-UHFFFAOYSA-N piperidin-3-amine Chemical compound NC1CCCNC1 PEUGKEHLRUVPAN-UHFFFAOYSA-N 0.000 claims description 2
- AKQXKEBCONUWCL-UHFFFAOYSA-N tert-butyl 3-aminopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC(N)C1 AKQXKEBCONUWCL-UHFFFAOYSA-N 0.000 claims description 2
- 108010000700 Acetolactate synthase Proteins 0.000 claims 1
- 241000588748 Klebsiella Species 0.000 claims 1
- NKSXDMWAVIOSTD-UHFFFAOYSA-N methyl 3-aminopent-2-enoate Chemical compound CCC(N)=CC(=O)OC NKSXDMWAVIOSTD-UHFFFAOYSA-N 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 8
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000013067 intermediate product Substances 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 229940127557 pharmaceutical product Drugs 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 229960003767 alanine Drugs 0.000 description 34
- NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 description 21
- 239000000370 acceptor Substances 0.000 description 20
- 238000011914 asymmetric synthesis Methods 0.000 description 20
- 102000007698 Alcohol dehydrogenase Human genes 0.000 description 19
- 108010021809 Alcohol dehydrogenase Proteins 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- 235000007682 pyridoxal 5'-phosphate Nutrition 0.000 description 19
- 239000011589 pyridoxal 5'-phosphate Substances 0.000 description 19
- 230000000694 effects Effects 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 10
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 10
- 239000002518 antifoaming agent Substances 0.000 description 10
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 9
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 9
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 8
- 241000607291 Vibrio fluvialis Species 0.000 description 8
- 241000588902 Zymomonas mobilis Species 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000588724 Escherichia coli Species 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 235000008170 thiamine pyrophosphate Nutrition 0.000 description 6
- 239000011678 thiamine pyrophosphate Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000005251 capillar electrophoresis Methods 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000012064 sodium phosphate buffer Substances 0.000 description 5
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 229940024606 amino acid Drugs 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000005891 transamination reaction Methods 0.000 description 4
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- 241001453369 Achromobacter denitrificans Species 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241001464780 Zymobacter palmae Species 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- STSLIPZQSYMYNW-UHFFFAOYSA-N methyl 3-aminopentanoate Chemical compound CCC(N)CC(=O)OC STSLIPZQSYMYNW-UHFFFAOYSA-N 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 241000607598 Vibrio Species 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000002210 biocatalytic effect Effects 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012847 fine chemical Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Chemical class 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- LOVUSASSMLUWRR-REOHCLBHSA-N (2s)-2-hydrazinylpropanoic acid Chemical compound NN[C@@H](C)C(O)=O LOVUSASSMLUWRR-REOHCLBHSA-N 0.000 description 1
- WTLNOANVTIKPEE-UHFFFAOYSA-N 2-acetyloxypropanoic acid Chemical compound OC(=O)C(C)OC(C)=O WTLNOANVTIKPEE-UHFFFAOYSA-N 0.000 description 1
- OQEBBZSWEGYTPG-UHFFFAOYSA-N 3-aminobutanoic acid Chemical compound CC(N)CC(O)=O OQEBBZSWEGYTPG-UHFFFAOYSA-N 0.000 description 1
- ASNHGEVAWNWCRQ-UHFFFAOYSA-N 4-(hydroxymethyl)oxolane-2,3,4-triol Chemical compound OCC1(O)COC(O)C1O ASNHGEVAWNWCRQ-UHFFFAOYSA-N 0.000 description 1
- 241000588986 Alcaligenes Species 0.000 description 1
- 102000004092 Amidohydrolases Human genes 0.000 description 1
- 108090000531 Amidohydrolases Proteins 0.000 description 1
- 241000233788 Arecaceae Species 0.000 description 1
- 241000193388 Bacillus thuringiensis Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- QIDNWZPEWXAZAZ-UHFFFAOYSA-N C1N=CC=CN1CC(=O)CN2CN=CC=C2 Chemical compound C1N=CC=CN1CC(=O)CN2CN=CC=C2 QIDNWZPEWXAZAZ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 108090000489 Carboxy-Lyases Proteins 0.000 description 1
- 102000004031 Carboxy-Lyases Human genes 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 102000004157 Hydrolases Human genes 0.000 description 1
- 108090000604 Hydrolases Proteins 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 229910014130 Na—P Inorganic materials 0.000 description 1
- 108091028043 Nucleic acid sequence Proteins 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 241000235070 Saccharomyces Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- PMIWXMLVUYTUDM-UHFFFAOYSA-N amino 2-oxopropanoate Chemical compound CC(=O)C(=O)ON PMIWXMLVUYTUDM-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 229940097012 bacillus thuringiensis Drugs 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 150000007523 nucleic acids Chemical group 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229960001327 pyridoxal phosphate Drugs 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YXVCLPJQTZXJLH-UHFFFAOYSA-N thiamine(1+) diphosphate chloride Chemical compound [Cl-].CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N YXVCLPJQTZXJLH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/10—Nitrogen as only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/10—Transferases (2.)
- C12N9/1096—Transferases (2.) transferring nitrogenous groups (2.6)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/001—Amines; Imines
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/06—Alanine; Leucine; Isoleucine; Serine; Homoserine
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/22—Tryptophan; Tyrosine; Phenylalanine; 3,4-Dihydroxyphenylalanine
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y206/00—Transferases transferring nitrogenous groups (2.6)
- C12Y206/01—Transaminases (2.6.1)
- C12Y206/01018—Beta-alanine-pyruvate transaminase (2.6.1.18)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06002859A EP1818411A1 (en) | 2006-02-13 | 2006-02-13 | Process for the preparation of optically active chiral amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2767898T3 true ES2767898T3 (es) | 2020-06-18 |
Family
ID=36686005
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10002780T Active ES2767898T3 (es) | 2006-02-13 | 2007-02-13 | Proceso para la preparación de una amina quiral ópticamente activa |
| ES07711521T Active ES2345734T3 (es) | 2006-02-13 | 2007-02-13 | Proceso para la preparacion de aminas quirales opticamente activas. |
| ES10002779.6T Active ES2626645T3 (es) | 2006-02-13 | 2007-02-13 | Proceso para la preparación de aminopirrolidinas quirales ópticamente activas (3-AP, B3-AP) |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07711521T Active ES2345734T3 (es) | 2006-02-13 | 2007-02-13 | Proceso para la preparacion de aminas quirales opticamente activas. |
| ES10002779.6T Active ES2626645T3 (es) | 2006-02-13 | 2007-02-13 | Proceso para la preparación de aminopirrolidinas quirales ópticamente activas (3-AP, B3-AP) |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US9074228B2 (da) |
| EP (4) | EP1818411A1 (da) |
| JP (2) | JP5430945B2 (da) |
| KR (1) | KR101294499B1 (da) |
| CN (1) | CN101384723B (da) |
| AT (1) | ATE469233T1 (da) |
| AU (1) | AU2007214717B2 (da) |
| BR (1) | BRPI0707454A2 (da) |
| CA (1) | CA2637821A1 (da) |
| DE (1) | DE602007006765D1 (da) |
| DK (1) | DK1987152T3 (da) |
| EA (1) | EA017070B1 (da) |
| ES (3) | ES2767898T3 (da) |
| IL (3) | IL192637A (da) |
| MX (1) | MX2008010416A (da) |
| PT (1) | PT1987152E (da) |
| WO (1) | WO2007093372A1 (da) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1818411A1 (en) * | 2006-02-13 | 2007-08-15 | Lonza AG | Process for the preparation of optically active chiral amines |
| EP2022852B8 (en) * | 2006-05-29 | 2017-08-23 | Kaneka Corporation | Method for production of optically active amine compound, recombinant vector, and transformant carrying the vector |
| TWI433674B (zh) | 2006-12-28 | 2014-04-11 | Infinity Discovery Inc | 環杷明（ｃｙｃｌｏｐａｍｉｎｅ）類似物類 |
| DE102007042600A1 (de) * | 2007-09-07 | 2009-03-12 | Evonik Degussa Gmbh | Verfahren zur Herstellung von enantiomerenangereichten Aminen |
| DE102007060705A1 (de) * | 2007-12-17 | 2009-06-18 | Evonik Degussa Gmbh | ω-Aminocarbonsäuren oder ihre Lactame, herstellende, rekombinante Zellen |
| AU2008345097A1 (en) | 2007-12-27 | 2009-07-09 | Infinity Pharmaceuticals, Inc. | Methods for stereoselective reduction |
| US8470564B2 (en) | 2009-01-08 | 2013-06-25 | Codexis, Inc. | Transaminase polypeptides |
| EP2401366B1 (en) | 2009-02-26 | 2013-12-18 | Codexis, Inc. | Transaminase biocatalysts |
| RU2011142780A (ru) * | 2009-03-23 | 2013-04-27 | Аминолюкс, Инк. | Способ получения оптически чистых аминокислот |
| ES2644992T3 (es) | 2009-06-22 | 2017-12-01 | Codexis, Inc. | Reacciones de transaminasa |
| JP6141015B2 (ja) * | 2009-08-05 | 2017-06-07 | インフィニティ ファーマスーティカルズ、インク． | シクロパミン類似体の酵素によるアミノ基転移 |
| EA022764B1 (ru) * | 2009-09-02 | 2016-02-29 | Лонца Аг | СПОСОБ ИДЕНТИФИКАЦИИ И ПОЛУЧЕНИЯ (R)-СПЕЦИФИЧЕСКОЙ ω-ТРАНСАМИНАЗЫ |
| DK2582799T3 (da) | 2010-06-17 | 2018-02-12 | Codexis Inc | Biokatalysatorer og fremgangsmåder til syntesen af (s)-3-(1-aminoethyl)-phenol |
| US8932836B2 (en) | 2010-08-16 | 2015-01-13 | Codexis, Inc. | Biocatalysts and methods for the synthesis of (1R,2R)-2-(3,4-dimethoxyphenethoxy)cyclohexanamine |
| US9394313B2 (en) | 2010-09-14 | 2016-07-19 | Infinity Pharmaceuticals, Inc. | Transfer hydrogenation of cyclopamine analogs |
| EP2623595B1 (en) | 2010-09-28 | 2016-11-02 | Kaneka Corporation | Novel transaminase showing high activity for glutamic acid, gene encoding same, and method for utilization thereof |
| EP2684953B1 (en) | 2011-03-11 | 2017-06-28 | Kaneka Corporation | Modified aminotransferase, gene thereof, and method for producing optically active amino compound using same |
| KR101479718B1 (ko) | 2012-07-06 | 2015-01-08 | 연세대학교 산학협력단 | 오메가 트랜스아미나아제의 조기질 순환을 이용한 광학 활성 아미노산의 제조방법 |
| WO2014060571A1 (en) * | 2012-10-18 | 2014-04-24 | Sandoz Ag | A process for preparing indoline derivatives |
| KR101493311B1 (ko) * | 2012-12-13 | 2015-02-16 | 연세대학교 산학협력단 | 광학 활성 아민 및 호모알라닌의 제조방법 |
| US9777301B2 (en) | 2012-12-13 | 2017-10-03 | Industry-Academic Cooperation Foundation, Yonsei University | Method for producing optically active amine compounds by deracemization |
| KR101479717B1 (ko) * | 2013-02-27 | 2015-01-08 | 연세대학교 산학협력단 | 트랜스아미나제를 이용한 광학활성 알킬아민과 아릴알킬아민의 동시생산방법 |
| KR101910259B1 (ko) | 2013-11-26 | 2018-12-19 | 아심켐 래보러토리즈 (톈진) 컴퍼니, 리미티드 | 트랜스아미나제 및 그 응용 |
| CN103865964A (zh) * | 2014-03-14 | 2014-06-18 | 上海朴颐化学科技有限公司 | 转氨酶法合成(r)-3-氨基哌啶的方法 |
| CA2988289C (en) | 2015-06-04 | 2023-12-05 | PellePharm, Inc. | Topical formulations for delivery of hedgehog inhibitor compounds and use thereof |
| CN105112468B (zh) * | 2015-10-14 | 2019-01-08 | 厦门大学 | 一种多酶耦联体系制备手性胺的方法 |
| CN105200089B (zh) * | 2015-10-15 | 2018-09-11 | 江苏暨明医药科技有限公司 | (s)-1-叔丁氧羰基-3-羟基哌啶制备方法及其装置 |
| CN116121315A (zh) | 2016-03-02 | 2023-05-16 | 巴斯夫欧洲公司 | 制造l-草胺膦的方法 |
| CN111349667B (zh) * | 2016-11-01 | 2022-05-06 | 凯莱英医药集团（天津）股份有限公司 | 一种手性氨基杂环化合物及其衍生物的制备方法 |
| WO2018207888A1 (ja) * | 2017-05-10 | 2018-11-15 | 株式会社カネカ | ラメルテオンの製造法 |
| CN107805648B (zh) * | 2017-10-10 | 2020-09-11 | 凯莱英生命科学技术(天津)有限公司 | 制备具有多个手性中心的胺化合物的方法 |
| US12559777B2 (en) | 2018-09-05 | 2026-02-24 | Basf Se | Methods for improving yields of L-glufosinate |
| CN109370998B (zh) * | 2018-11-30 | 2020-08-04 | 江南大学 | 一种催化效率提高的ω-转氨酶突变体I215F |
| CN110724675B (zh) * | 2019-10-31 | 2021-02-02 | 宁波酶赛生物工程有限公司 | 转氨酶催化剂和酶法合成(r)-1-叔丁氧羰基-3-氨基哌啶的方法 |
| CN112626142B (zh) * | 2020-12-17 | 2022-10-18 | 永农生物科学有限公司 | 利用生物多酶偶联法制备l-草铵膦的方法 |
| CN114657164B (zh) * | 2020-12-17 | 2024-04-09 | 永农生物科学有限公司 | (s)-转氨酶及其应用 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3482982D1 (de) | 1983-09-01 | 1990-09-20 | Genetics Inst | Herstellung von l-aminosaeuren durch transaminierung. |
| DE3786707D1 (de) | 1986-06-04 | 1993-09-02 | Hoechst Ag | Verfahren zur herstellung von l-phosphinothricin durch transaminierung. |
| JPS63304986A (ja) | 1987-06-04 | 1988-12-13 | Daicel Chem Ind Ltd | プラスミド |
| JPH0787778B2 (ja) | 1987-12-10 | 1995-09-27 | 田辺製薬株式会社 | 新規微生物及びそれを用いるｌ−アミノ酸の製法 |
| US5424202A (en) | 1988-08-31 | 1995-06-13 | The University Of Florida | Ethanol production by recombinant hosts |
| US4950606A (en) * | 1989-06-22 | 1990-08-21 | Celgene Corporation | Enantiomeric enrichment and stereoselective synthesis of chiral amines |
| US5300437A (en) * | 1989-06-22 | 1994-04-05 | Celgene Corporation | Enantiomeric enrichment and stereoselective synthesis of chiral amines |
| US6197558B1 (en) | 1997-05-19 | 2001-03-06 | Nsc Technologies | Transaminase biotransformation process |
| IL125658A0 (en) | 1997-08-18 | 1999-04-11 | Hoffmann La Roche | Ccr-3 receptor antagonists |
| CA2322605A1 (en) * | 1998-03-11 | 1999-09-16 | Celgro | Improvements in the enzymatic synthesis of chiral amines |
| DE19919848A1 (de) * | 1999-04-30 | 2000-11-02 | Aventis Cropscience Gmbh | Verfahren zur Herstellung von L-Phosphinothricin durch enzymatische Transaminierung mit Aspartat |
| AU2001292094A1 (en) | 2000-10-06 | 2002-04-15 | Elsworth Biotechnology Limited | Ethanol production |
| US6576794B2 (en) * | 2000-12-28 | 2003-06-10 | Kao Corporation | Process for production of ether amine |
| TWI377253B (en) | 2001-04-16 | 2012-11-21 | Martek Biosciences Corp | Product and process for transformation of thraustochytriales microorganisms |
| JP4459807B2 (ja) | 2002-04-29 | 2010-04-28 | メルク エンド カムパニー インコーポレーテッド | テトラヒドロピラニルシクロペンチルテトラヒドロイソキノリン系のケモカイン受容体活性調節剤 |
| DE60308204T2 (de) * | 2002-08-01 | 2007-08-23 | Basilea Pharmaceutica Ag | Verfahren zur herstellung von aminopyrrolidinderivaten |
| DE602005022188D1 (de) | 2004-04-27 | 2010-08-19 | Archer Daniels Midland Co | Enzymatische decarboxylierung von 2-keto-l-gulonsäure zur herstellung von xylose |
| US8133705B2 (en) * | 2005-05-23 | 2012-03-13 | Kaneka Corporation | Aminotransferase, gene encoding the same, and method of using them |
| EP1818411A1 (en) * | 2006-02-13 | 2007-08-15 | Lonza AG | Process for the preparation of optically active chiral amines |
| EP1897956A1 (en) * | 2006-09-06 | 2008-03-12 | Lonza AG | Process for preparation of optically active amines by optical resolution of racemic amines employing a bacterial omega-transaminase |
-
2006
- 2006-02-13 EP EP06002859A patent/EP1818411A1/en not_active Withdrawn
-
2007
- 2007-02-13 KR KR1020087019720A patent/KR101294499B1/ko not_active Expired - Fee Related
- 2007-02-13 EP EP07711521A patent/EP1987152B1/en not_active Not-in-force
- 2007-02-13 BR BRPI0707454-9A patent/BRPI0707454A2/pt not_active IP Right Cessation
- 2007-02-13 AT AT07711521T patent/ATE469233T1/de not_active IP Right Cessation
- 2007-02-13 DE DE602007006765T patent/DE602007006765D1/de active Active
- 2007-02-13 CN CN2007800052396A patent/CN101384723B/zh not_active Expired - Fee Related
- 2007-02-13 EP EP10002780.4A patent/EP2202318B1/en active Active
- 2007-02-13 MX MX2008010416A patent/MX2008010416A/es active IP Right Grant
- 2007-02-13 ES ES10002780T patent/ES2767898T3/es active Active
- 2007-02-13 PT PT07711521T patent/PT1987152E/pt unknown
- 2007-02-13 EA EA200870262A patent/EA017070B1/ru not_active IP Right Cessation
- 2007-02-13 AU AU2007214717A patent/AU2007214717B2/en not_active Ceased
- 2007-02-13 US US12/223,730 patent/US9074228B2/en not_active Expired - Fee Related
- 2007-02-13 JP JP2008554659A patent/JP5430945B2/ja not_active Expired - Fee Related
- 2007-02-13 CA CA002637821A patent/CA2637821A1/en not_active Abandoned
- 2007-02-13 ES ES07711521T patent/ES2345734T3/es active Active
- 2007-02-13 EP EP10002779.6A patent/EP2202317B1/en not_active Not-in-force
- 2007-02-13 DK DK07711521.0T patent/DK1987152T3/da active
- 2007-02-13 ES ES10002779.6T patent/ES2626645T3/es active Active
- 2007-02-13 WO PCT/EP2007/001222 patent/WO2007093372A1/en not_active Ceased
-
2008
- 2008-07-06 IL IL192637A patent/IL192637A/en not_active IP Right Cessation
-
2012
- 2012-04-15 IL IL219163A patent/IL219163A0/en unknown
- 2012-04-15 IL IL219164A patent/IL219164A0/en unknown
-
2013
- 2013-05-08 JP JP2013098609A patent/JP2013188217A/ja active Pending
-
2015
- 2015-06-16 US US14/740,646 patent/US9551018B2/en not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2767898T3 (es) | Proceso para la preparación de una amina quiral ópticamente activa | |
| JP5102297B2 (ja) | 細菌性オメガアミノ基転移酵素を利用したラセミアミン混合物の光学的分解能による光学活性ｎ−保護３−アミノピロリジン又は光学活性ｎ−保護３−アミノピペリジン及び対応するケトンの調製方法 | |
| CN107119084A (zh) | 一种利用转氨酶和乙烯合成酶生产l‑草铵膦的方法 | |
| Schirch et al. | Drug Discovery, Virginia Commonwealth University, Richmond, Virginia 23298 | |
| JPS61195696A (ja) | Ｌ−フエニルアラニンの製造方法 |